HCID 57085542, compound → HCID 70569826, compound

Participants

Reaction Conditions

Reaction Steps

A slurry of copper iodide (8.63 g, 0.045 mol) in 250 ml of anhydrous diethyl ether was cooled at -20° to -25° C. in a dry ice/carbon tetrachloride bath while being held under a nitrogen atmosphere. Methyl lithium (49.3 ml of a 1.84 M solution in ether, 0.091 mol) was cannulated into a calibrated dropping funnel and quickly added to the slurry. This complex was cooled an additional 10 minutes at -25° C. before a solution of 7,8-didehydro-3,14-dimethoxy-17-methylmorphinan-6-one (3) (9.47 g, 0.032 mol) in 60 ml of dry methylene chloride was added dropwise and washed in with an additional 30 ml of dry diethyl ether. After stirring at -20° C. for 21/2 hours, the reaction mixture was quenched with 60 ml of 20% ammonium hydroxide and made basic by the addition of 50% sodium hydroxide. The resultant copper salts were removed by suction filtration and the filter cake was washed several times with diethyl ether and water. The layers were separated and the aqueous phase extracted with two additional portions of ether. The ethereal extracts were combined, washed with saturated sodium chloride solution, dried over Na2SO4 and concentrated under reduced pressure. Purification by chromatography on Flosisil (eluted with graded methanol/chloroform) yielded 4.6 g (46% theory) of the title compound.

Provenance & Evidence